diacerein   Click here for help

GtoPdb Ligand ID: 10800

Synonyms: Artrodar® | Fisiodar®
Approved drug
diacerein is an approved drug
Compound class: Synthetic organic
Comment: Diacerein is a prodrug which is metabolized to rhein. It has anti-inflammatory activity via antagonism of the interleukin-1 receptor. It is an anthraquinone type compound and growth-inhibitory effects of diacerein have been shown against various drug-resistant staphylococcal strains [2].

diacerein is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 124.04
Molecular weight 368.05
XLogP 2.29
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
Isomeric SMILES CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
InChI InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)
InChI Key TYNLGDBUJLVSMA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5371 diacerein
Synonyms Click here for help
Artrodar® | Fisiodar®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Diacerein
Other databases
CAS Registry No. 13739-02-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL41286
DrugCentral Ligand 849
GtoPdb PubChem SID 405560241
PubChem CID 26248
Search Google for chemical match using the InChIKey TYNLGDBUJLVSMA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone TYNLGDBUJLVSMA
Search PubMed clinical trials diacerein
Search PubMed titles diacerein
Search PubMed titles/abstracts diacerein
UniChem Compound Search for chemical match using the InChIKey TYNLGDBUJLVSMA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TYNLGDBUJLVSMA-UHFFFAOYSA-N

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MedChemExpress
Diacerein (links to external site)
Cat. No. HY-N0283